6-chloro-3-hydroxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran | 1229-59-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-chloro-3-hydroxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran
• 英文别名: 6-chloro-3-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one；6-Chlor-4'-methoxyflavon-3-ol；6-Chlor-4'-methoxy-flavonol；6-Chloro-3-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 1229-59-0
• 化学式: C₁₆H₁₁ClO₄
• 分子量: 302.714
• InChiKey: OSHAVRCRDOTVTH-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  465.5±45.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-3-hydroxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran 在 三氟化硼乙醚 、 thallium(III) acetate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以94%的产率得到6-Chloro-3-hydroxy-2,3-dimethoxy-2-(4-methoxy-phenyl)-chroman-4-one
  参考文献：
  名称：

  Singh, Om V.; Khanna, Mahavir S.; Tanwar, Madan P., Synthetic Communications, 1990, vol. 20, # 16, p. 2401 - 2408

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以76%的产率得到6-chloro-3-hydroxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran
  参考文献：
  名称：

  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

  摘要：

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

  DOI：

  10.1021/jm00106a039

文献信息

• Synthesis, characterization and cytotoxicity studies of Co(III)-flavonolato complexes
  作者：Máté Kozsup、XueQuan Zhou、Etelka Farkas、Attila Cs. Bényei、Sylvestre Bonnet、Tamás Patonay、Krisztina Kónya、Péter Buglyó

  DOI：10.1016/j.jinorgbio.2021.111382

  日期：2021.4

  with a selective delivery of cytotoxic or antibacterial compounds. Whithin this field sixteen novel Co(III) ternary complexes with the general formula [Co(4N)(flav)](ClO4)2, where 4N = tris(2-aminoethyl)amine (tren) or tris(2-pyridylmethyl)amine (tpa) and flav = deprotonated form of differently substituted flavonols have been synthesized, characterized, and their cytotoxicity assayed under both normoxic

  作为前药的缺氧活化的 Co(III) 复合物可以提供细胞毒性或抗菌化合物的选择性递送。在该领域内有十六种新型 Co(III) 三元配合物，通式为 [Co(4N)(flav)](ClO 4 ) 2, 其中 4N = 三 (2-氨基乙基) 胺 (tren) 或三 (2-吡啶基甲基) 胺 (tpa) 和 flav = 不同取代的黄酮醇的去质子化形式已被合成、表征并在常氧和缺氧条件下测定其细胞毒性. 还报道了两种游离黄酮醇和七种配合物的分子结构。在所有配合物中，生物配体表现出预期的 (O,O) 配位模式，并且配合物表现出略微扭曲的八面体几何形状。循环伏安研究表明，黄酮醇的取代基和 4N 供体配体的类型对复合物的还原电位都有影响。含有tren的那些表现出比tpa类似物显着更高的稳定性，使这些以前的化合物成为开发缺氧激活的前药复合物的有希望的候选者。Tpa 复合物对两种选定的人类癌细胞系（A549、A
• Oxidation of Flavonols Using Lead(IV) Acetate in Acidic Methanol
  作者：Devinder Kumar、Om V. Singh

  DOI：10.1080/00397919208019315

  日期：1992.5

  Abstract Oxidation of Flavonols (1a-h) and 6-propionyl-flavonols (1i-j) to 2,3-dimethoxy-3-hydroxyflavanones (2a-h) and 2,3-dimethoxy-3-hydroxyflavanones (2i-j), respectively using lead(IV) acetate in methanol in presence of perchloric acid and the mechanism of this transformation has been described.

  摘要 黄酮醇 (1a-h) 和 6-丙酰基-黄酮醇 (1i-j) 氧化为 2,3-二甲氧基-3-羟基黄烷酮 (2a-h) 和 2,3-二甲氧基-3-羟基黄烷酮 (2i-j) ，分别在高氯酸存在下在甲醇中使用乙酸铅（IV），并且已经描述了这种转化的机制。
• Absorption and Fluorescent Studies of 3-Hydroxychromones
  作者：Radhika Khanna、Ramesh Kumar、Aarti Dalal、Ramesh C. Kamboj

  DOI：10.1007/s10895-015-1623-0

  日期：2015.9

  The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N* and T* band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N* and T* band. Therefore, these 3-HCs may behave as the possible fluorescent probes.

  已经进行了各种取代的3-羟基色酮的合成和光谱研究。发现了合成的 3-羟基色酮 (3-HC) 的结构基序与其荧光特性之间的关键关系。 4'位被给电子基团取代的色酮表现出N*和T*带的红移，并且荧光强度比增加，而带有吸电子基团的色酮则表现出N*和T*带的蓝移。 T*带。因此，这些 3-HC 可能充当可能的荧光探针。
• Photoisomerization of allyl ethers: syntheses of vinyl ethers
  作者：Satish C Gupta、Mohamad Yusuf、Somesh Sharma、Surinder Arora

  DOI：10.1016/s0040-4039(02)01366-7

  日期：2002.9

  A synthesis of vinyl ethers through the photoisomerization of allyl ethers is described.

  描述了通过烯丙基醚的光异构化合成乙烯基醚的方法。
• Compounds for immunopotentiation
  申请人：Valiante Nicholas

  公开号：US20100226931A1

  公开（公告）日：2010-09-09

  Methods of stimulating an immune response and treating patients responsive thereto with 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-diones, staurosporine analogs, derivatized pyridazines, chromen-4-ones, indolinones, quinazolines, nucleoside analogs, and other small molecules are disclosed. In a preferred embodiment benzopyrimidine derivatives such as ZD-6474, MLN-518, lapatinib, gefitinib or erlotinib are used.

  本发明公开了刺激免疫反应和治疗对3,4-二（1H-吲哚-3-基）-1H-吡咯-2,5-二酮，链霉菌素类似物，衍生的吡啶并嗪，香豆素-4-酮，吲哚酮，喹唑啉，核苷类似物和其他小分子具有响应性的患者。在一种优选实施方式中，使用苯并嘧啶衍生物，例如ZD-6474，MLN-518，拉帕替尼，吉非替尼或厄洛替尼。